2,4,6-Triiodophenol → 2,4,6-Triiodophenyl (2-propyl)pentanoate

HRID 1741995

反応式

HRID 1741995 の反応式
[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].[CH2:11]([CH:14]([CH2:18][CH2:19]C)[C:15](Cl)=[O:16])[CH2:12][CH3:13].[C:21](=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:21][CH:18]([CH:14]([CH2:11][CH2:12][CH3:13])[C:15]([O:10][C:3]1[C:2]([I:1])=[CH:7][C:6]([I:8])=[CH:5][C:4]=1[I:9])=[O:16])[CH3:19]

参加物

6

反応物 3

HCID 118622,4,6-TriiodophenolHCID 762402-Propylvaleryl chlorideHCID 516892Sodium Bicarbonate

生成物 1

HCID 867478922,4,6-Triiodophenyl (2-propyl)pentanoate収率 68%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 2,4,6-triiodophenol (2.0 g, 4.24 mmol), 2-propylvaleroyl chloride (2.5 ml, 12.7 mmol, 3 eq) and 4-dimethylaminopyridine (DMAP; 20 mg) in 20 ml of acetonitrile was refluxed under argon overnite. The reaction mixture was cooled and poured into excess aqueous sodium bicarbonate and then extracted with dichloromethane. The dichloromethane extract was dried over magnesium sulfate, filtered, and evaporated to give the crude product (2.42 mmol, 95%) as a pink solid. Recrystallization from ethyl acetate gave 1.75 g (68%) of pure product, mp 99°-101° C.

後処理

  1. temperaturewas refluxed under argon overnite
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. extractionThe dichloromethane extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product (2.42 mmol, 95%) as a pink solid
  9. customRecrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-1d8b5c1a325a4bee9e58a464aa9e8eda
出典データセット
uspto-grants-1994_08
特許番号
US05336484

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